Heterocyclylethylbenzamide derivatives

ABSTRACT

A compound of general formula (I): 
     
       
         
         
             
             
         
       
     
     A process for preparing this compound. 
     A fungicide composition comprising a compound of general formula (I). 
     A method for treating plants by applying a compound of general formula (I) or a composition comprising it.

CROSS-REFERENCE TO RELATED APPLICATIONS

The present application is a 35 U.S.C. §371 national phase conversion ofPCT/EP2006/061952 filed 2 May 2006, which claims priority of EuropeanApplication No. 05356075.1 filed 3 May 2005.

The present invention relates to novel heterocyclylethylbenzamidederivatives, their process of preparation, their use as fungicides,particularly in the form of fungicidal compositions, and methods for thecontrol of phytopathogenic fungi of plants using these compounds ortheir compositions.

International patent application WO 01/11965 discloses a broad family offungicidal compounds in which the 2-pyridyl group is substituted by atleast one halogenoalkyl group. This document does not disclose neitherit covers heterocyclylethylbenzamide derivatives according to thepresent invention.

It is always of high-interest in the field of agrochemicals to usepesticidal compounds to use novel pesticidal compounds in order to avoidor to fight the development of resistant strains to the activeingredients used by the farmer.

We have now found a new family of compounds which possess the abovementioned characteristics.

Accordingly, the present invention relates to aheterocyclylethylbenzamide derivative of general formula (I)

-   -   in which:    -   n is 1, 2, 3, 4 or 5;    -   p is 1, 2, 3 or 4;    -   A represents a 6-membered non-fused heterocycle with one, two or        three heteroatoms which may be the same or different, provided        that A is different from pyridyl, piperidine and piperazine;    -   z is a carbon atom or a heteroatom which can not be substituted        by X;    -   X is the same or different and is a halogen atom, a nitro group,        a cyano group, a hydroxy group, an amino group, a sulfanyl        group, a pentafluoro-λ⁶-sulfanyl group, a formyl group, a        formyloxy group, a formylamino group, a carboxy group, a        carbamoyl group, a N-hydroxycarbamoyl group, a carbamate group,        a (hydroxyimino)-C₁-C₆-alkyl group, a C₁-C₈-alkyl, a        C₂-C₈-alkenyl, a C₂-C₈-alkynyl, a C₁-C₈-alkylamino, a        C₁-C₈-halogenoalkyl having 1 to 5 halogen atoms, a        di-C₁-C₈-alkylamino, a C₁-C₈-alkoxy, a C₁-C₈-halogenoalkoxy        having 1 to 5 halogen atoms, a C₁-C₈-alkylsulfanyl, a        C₁-C₈-halogenoalkylsulfanyl having 1 to 5 halogen atoms, a        C₂-C₈-alkenyloxy, a C₂-C₈-halogenoalkenyloxy having 1 to 5        halogen atoms, a C₃-C₈-alkynyloxy, a C₃-C₈-halogenoalkynyloxy        having 1 to 5 halogen atoms, a C₃-C₈-cycloalkyl, a        C₃-C₈-halogenocycloalkyl having 1 to 5 halogen atoms, a        C₁-C₈-alkylcarbonyl, a C₁-C₈-halogenoalkylcarbonyl having 1 to 5        halogen atoms, a C₁-C₈-alkylcarbamoyl, a        di-C₁-C₈-alkylcarbamoyl, a N—C₁-C₈-alkyloxycarbamoyl, a        C₁-C₈-alkoxycarbamoyl, a N—C₁-C₈-alkyl-C₁-C₈-alkoxycarbamoyl, a        C₁-C₈-alkoxycarbonyl, a C₁-C₈-halogenoalkoxycarbonyl having 1 to        5 halogen atoms, a C₁-C₈-alkylcarbonyloxy, a        C₁-C₈-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, a        C₁-C₈-alkylcarbonylamino, a C₁-C₈-halogenoalkylcarbonylamino        having 1 to 5 halogen atoms, a C₁-C₈-alkylaminocarbonyloxy, a        di-C₁-C₈-alkylaminocarbonyloxy, a C₁-C₈-alkyloxycarbonyloxy, a        C₁-C₈-alkylsulphenyl, a C₁-C₈-halogenoalkylsulphenyl having 1 to        5 halogen atoms, a C₁-C₈-alkylsulphinyl, a        C₁-C₈-halogenoalkylsulphinyl having 1 to 5 halogen atoms, a        C₁-C₈-alkylsulphonyl, a C₁-C₈-halogenoalkylsulphonyl having 1 to        5 halogen atoms, a C₁-C₆-alkoxyimino, a        (C₁-C₆-alkoxyimino)-C₁-C₆-alkyl, a        (C₁-C₆-alkenyloxyimino)C₁-C₆-alkyl, a        (C₁-C₆-alkynyloxyimino)-C₁-C₆-alkyl, a        benzyloxyimino)-C₁-C₆-alkyl, a benzyloxy, a benzylsulfanyl, a        benzylamino, a phenoxy, a phenylsulfanyl a phenyl or a        phenylamino;    -   R¹ and R² are the same or different and are a hydrogen atom, a        hydrogen atom, a cyano group, a formyl group, a carboxy group, a        carbamoyl group, a (hydroxyimino)-C₁-C₆-alkyl group, a        C₁-C₈-alkyl, C₃-C₇-cycloalkyl-C₁-C₈-alkyl, a C₂-C₈-alkenyl, a        C₂-C₈-alkynyl, a C₃-C₈-cycloalkyl, a C₃-C₈-halogenocycloalkyl        having 1 to 5 halogen atoms, a C₁-C₈-alkylcarbonyl, a        C₁-C₈-halogenoalkylcarbonyl having 1 to 5 halogen atoms, a        C₁-C₈-halogenoalkyl having 1 to 5 halogen atoms, a        C₁-C₈-alkylcarbamoyl, a di-C₁-C₈-alkylcarbamoyl, a        C₁-C₈-alkoxycarbamoyl, a C₁-C₈-alkoxycarbonyl or a        C₁-C₈-halogenoalkoxycarbonyl having 1 to 5 halogen atoms;    -   R³ and R⁴ are the same or different and are a hydrogen atom, a        cyano group, a formyl group, a carboxy group, a carbamoyl group,        a (hydroxyimino)-C₁-C₆-alkyl group, a C₁-C₈-alkyl, a        C₃-C₇-cycloalkyl-C₁-C₈-alkyl, a C₂-C₈-alkenyl, a C₂-C₈-alkynyl,        a C₃-C₈-cycloalkyl, a C₃-C₈-halogenocycloalkyl having 1 to 5        halogen atoms, a C₁-C₈-alkylcarbonyl, a        C₁-C₈-halogenoalkylcarbonyl having 1 to 5 halogen atoms, a        C₁-C₉-halogenoalkyl having 1 to 5 halogen atoms, a        C₁-C₈-alkylcarbamoyl, a di-C₁-C₈-alkylcarbamoyl, a        C₁-C₈-alkoxycarbamoyl, a C₁-C₈-alkoxycarbonyl or a        C₁-C₈-halogenoalkoxycarbonyl having 1 to 5 halogen atoms;    -   R⁵ is a hydrogen atom, a C₁-C₆-alkyl, or a C₃-C₇-cycloalkyl;    -   Y is the same or different and is a hydrogen atom, a halogen        atom, a nitro group, a cyano group, a hydroxy group, an amino        group, a sulfanyl group, a pentafluoro-λ⁶-sulfanyl group, a        formyl group, a formyloxy group, a formylamino group, a carboxy        group, a carbamoyl group, a N-hydroxycarbamoyl group, a        carbamate group, a (hydroxyimino)-C₁-C₆-alkyl group, a        C₁-C₉-alkyl, a C₂-C₈-alkenyl, a C₂-C₈-alkynyl, a C₁-C₈-alkoxy, a        C₁-C₈-halogenoalkyl having 1 to 5 halogen atoms, a        C₁-C₈-alkylsulfanyl, a C₁-C₈-halogenoalkylsulfanyl having 1 to 5        halogen atoms, a C₂-C₈-alkenyloxy, a C₂-C₈-halogenoalkenyloxy        having 1 to 5 halogen atoms, a C₃-C₈-alkynyloxy, a        C₃-C₈-halogenoalkynyloxy having 1 to 5 halogen atoms, a        C₃-C₈-cycloalkyl, a C₃-C₈-halogenocycloalkyl having 1 to 5        halogen atoms, a C₁-C₈-alkylcarbonyl, a        C₁-C₈-halogenoalkylcarbonyl having 1 to 5 halogen atoms, a        C₁-C₈-alkylcarbamoyl, a di-C₁-C₈-alkylcarbamoyl, a        N—C₁-C₈-alkyloxycarbamoyl, a C₁-C₈-alkoxycarbamoyl, a        N—C₁-C₈-alkyl-C₁-C₈-alkoxycarbamoyl, a C₁-C₈-alkoxycarbonyl, a        C₁-C₈-halogenoalkoxycarbonyl having 1 to 5 halogen atoms, a        C₁-C₈-alkylcarbonyloxy, a C₁-C₈-halogenoalkylcarbonyloxy having        1 to 5 halogen atoms, a C₁-C₈-alkylcarbonylamino, a        C₁-C₈-halogenoalkylcarbonylamino having 1 to 5 halogen atoms, a        C₁-C₈-alkylaminocarbonyloxy, a di-C₁-C₈-alkylaminocarbonyloxy, a        C₁-C₈-alkyloxycarbonyloxy, a C₁-C₈-alkylsulphenyl, a        C₁-C₈-halogenoalkylsulphenyl having 1 to 5 halogen atoms, a        C₁-C₈-alkylsulphinyl, a C₁-C₈-halogenoalkylsulphinyl having 1 to        5 halogen atoms, a C₁-C₈-alkylsulphonyl, a        C₁-C₈-halogenoalkyl-sulphonyl having 1 to 5 halogen atoms, a        C₁-C₆-alkoxyimino, a (C₁-C₆-alkoxyimino)-C₁-C₆-alkyl, a        (C₁-C₆-alkenyloxyimino)C₁-C₆-alkyl, a        (C₁-C₆-alkynyloxyimino)-C₁-C₆-alkyl, a        (benzyloxyimino)-C₁-C₆-alkyl; and    -   Y^(a) is a halogen atom, a cyano group, a sulfanyl group, a        pentafluoro-λ⁶-sulfanyl group, a formyl group, a formyloxy        group, a formylamino group, a carbamoyl group, a        N-hydroxycarbamoyl group, a carbamate group, a        (hydroxyimino)-C₁-C₆-alkyl group, a C₁-C₈-alkyl, a        C₂-C₈-alkenyl, a C₂-C₈-alkynyl, a C₁-C₈-alkoxy, a        C₁-C₈-halogenoalkyl having 1 to 5 halogen atoms, a        C₁-C₈-halogenoalkoxy having 1 to 5 halogen atoms, a        C₁-C₈-alkylsulfanyl, a C₁-C₈-halogenoalkylsulfanyl having 1 to 5        halogen atoms, a C₂-C₈-halogenoalkenyloxy having 1 to 5 halogen        atoms, a C₃-C₈-alkynyloxy, a C₃-C₈-halogenoalkynyloxy having 1        to 5 halogen atoms, a C₃-C₈-cycloalkyl, a        C₃-C₈-halogenocycloalkyl having 1 to 5 halogen atoms, a        C₁-C₈-alkylcarbonyl, a C₁-C₈-halogenoalkylcarbonyl having 1 to 5        halogen atoms, a C₁-C₈-alkylcarbamoyl, a        di-C₁-C₈-alkylcarbamoyl, a N—C₁-C₈-alkyloxycarbamoyl, a        C₁-C₉-alkoxycarbamoyl, a N—C₁-C₈-alkyl-C₁-C₈-alkoxycarbamoyl, a        C₁-C₈-alkoxycarbonyl, a C₁-C₈-halogenoalkoxycarbonyl having 1 to        5 halogen atoms, a C₁-C₈-alkylcarbonyloxy, a        C₁-C₈-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, a        C₁-C₈-alkylcarbonylamino, a C₁-C₈-halogenoalkylcarbonylamino        having 1 to 5 halogen atoms, a C₁-C₈-alkylaminocarbonyloxy, a        di-C₁-C₈-alkylaminocarbonyloxy, a C₁-C₈-alkyloxycarbonyloxy, a        C₁-C₈-alkylsulphenyl, a C₁-C₈-halogenoalkylsulphenyl having 1 to        5 halogen atoms, a C₁-C₈-alkylsulphinyl, a        C₁-C₈-halogenoalkylsulphinyl having 1 to 5 halogen atoms, a        C₁-C₈-alkylsulphonyl, a C₁-C₈-halogenoalkyl-sulphonyl having 1        to 5 halogen atoms, a C₁-C₆-alkoxyimino, a        (C₁-C₆-alkoxyimino)-C₁-C₆-alkyl, a        (C₁-C₆-alkenyloxyimino)-C₁-C₆-alkyl, a        (C₁-C₆-alkynyloxyimino)-C₁-C₆-alkyl, a        (benzyloxyimino)-C₁-C₆-alkyl;

as well as its salts, N-oxydes, metallic complexes, metalloidiccomplexes and optically active isomers.

In the context of the present invention:

halogen means fluorine, bromine, chlorine or iodine.

carboxy means —C(═O)OH; carbonyl means —C(═O)—; carbamoyl means—C(═O)NH₂; N-hydroxycarbamoyl means —C(═O)NHOH;

an alkyl group, an alkenyl group, and an alkynyl group as well asmoieties containing these terms, can be linear or branched; and

heteroatom means sulphur, nitrogen or oxygen.

In the context of the present invention, it has also to be understoodthat in the case of di-substituted amino and of di-substituted carbamoylradicals, the two substituents may form together with the nitrogen atombearing them a saturated heterocyclic ring containing 3 to 7 atoms.

Any of the compounds of the present invention can exist in one or moreoptical or chiral isomer forms depending on the number of asymmetriccentres in the compound. The invention thus relates equally to all theoptical isomers and to their racemic or scalemic mixtures (the term“scalemic” denotes a mixture of enantiomers in different proportions),and to the mixtures of all the possible stereoisomers, in allproportions. The diastereoisomers and/or the optical isomers can beseparated according to the methods which are known per se by the manordinary skilled in the art.

Any of the compounds of the present invention can also exist in one ormore geometric isomer forms depending on the number of double bonds inthe compound. The invention thus relates equally to all geometricisomers and to all possible mixtures, in all proportions. The geometricisomers can be separated according to general methods, which are knownper se by the man ordinary skilled in the art.

Any of the compounds of general formula (I) wherein X represents ahydroxy, a sulfanyl group or an amino group may be found in itstautomeric form resulting from the shift of the proton of said hydroxy,sulfanyl or amino group. Such tautomeric forms of such compounds arealso part of the present invention. More generally speaking, alltautomeric forms of compounds of general formula (I) wherein Xrepresents a hydroxy, a sulfanyl group or an amino group, as well as thetautomeric forms of the compounds which can optionally be used asintermediates in the preparation processes, and which will be defined inthe description of these processes, are also part of the presentinvention.

According to the present invention, the “A” group may be substituted inany position by (X)_(n), in which X and n are as defined above.Preferably, the present invention relates to heterocyclylethylbenzamidederivative of general formula (I) in which the different characteristicsmay be chosen alone or in combination as being:

as regards n, n is 1 or 2;

as regards X, X is chosen as being a methyl group, a halogen atom orC₁-C₈-halogenoalkyl having 1 to 5 halogen atoms. More preferably, X is ahalogen atom.

According to the present invention, the carbon atoms of the carboxamidemoiety of the compound of formula (I) are substituted by R¹, R², R³ andR⁴; R¹, R², R³ and R⁴ being as defined above. Preferably, the presentinvention also relates to heterocyclylethylbenzamide derivative ofgeneral formula (I) in which the different characteristics may be chosenalone or in combination as being:

as regards R¹ and R², R¹ and R² are chosen, independently of each other,as being a hydrogen atom, a C₁-C₈-alkyl, a C₂-C₈-alkenyl, aC₂-C₈-alkynyl, a C₃-C₈-cycloalkyl, a C₃-C₇-cycloalkyl-C₁-C₈-alkyl, aC₃-C₈-halogenocycloalkyl having 1 to 5 halogen atoms or aC₁-C₈-halogenoalkyl having 1 to 5 halogen atoms;

as regards R³ and R⁴, R³ and R⁴ are chosen, independently of each other,as being a hydrogen atom, a C₁-C₈-alkyl, a C₂-C₈-alkenyl, aC₂-C₈-alkynyl, a C₃-C₈-cycloalkyl, a C₃-C₇-cycloalkyl-C₁-C₈-alkyl, aC₃-C₈-halogenocycloalkyl having 1 to 5 halogen atoms or aC₁-C₈-halogenoalkyl having 1 to 5 halogen atoms.

According to the present invention, the nitrogen atom of the carboxamidemoiety of the compound of formula (I) is substituted by R⁵, R⁵ being ahydrogen atom, a C₁-C₆-alkyl or a C₃-C₇-cycloalkyl. Preferably, theC₃-C₇-cycloalkyl is cyclopropyl.

According to the present invention, the phenyl moiety is substituted inortho position by Y^(a) and may be substituted in any other position by(Y)_(p), in which Y^(a), Y and p are as defined above. Preferably, thepresent invention relates to heterocyclylethylbenzamide derivative ofgeneral formula (I) in which the different characteristics may be chosenalone or in combination as being:

as regards Y^(a), Y^(a) is chosen as being a halogen atom, apentafluoro-λ⁶-sulfanyl group, a C₁-C₈-alkyl, a C₁-C₈-halogenoalkylhaving 1 to 5 halogen atoms or a C₁-C₈-halogenoalkoxy having 1 to 5halogen atoms;

as regards p, p is 1;

as regards Y, Y is chosen as being a hydrogen atom or a halogen atom.More preferably Y is a hydrogen atom.

According to the present invention, the “A” group of the compound ofgeneral formula (I) is a six membered ring non-fused heterocycle withone, two or three heteroatoms which may be the same or different.Preferably, the present invention also relates toheterocyclylethylbenzamide derivative of general formula (I) in whichthe different characteristics may be chosen alone or in combination asbeing:

A is chosen as being a pyridazine, a pyrimidine or a pyrazine. Morepreferably, A is a pyrimidine;

A is substituted in ortho position.

Specific examples of “A” group include:

A represents a heterocycle of the general formula (A-1)

-   -   in which:    -   R⁶ may be a halogen atom, a hydroxy group, a cyano group, a        C₁-C₄-alkyl, a C₁-C₄-halogenoalkyl having 1 to 5 halogen atoms,        a C₁-C₄-alkoxy, a C₁-C₄-alkylthio, a C₁-C₄-halogenoalkylthio        having 1 to 5 halogen atoms or a C₁-C₄-halogenoalkoxy having 1        to 5 halogen atoms;    -   R⁷ may be a hydrogen atom, a C₁-C₄-alkyl, a C₁-C₄-halogenoalkyl        having 1 to 5 halogen atoms or a benzyl.

A represents a heterocycle of the general formula (A-2)

-   -   in which:    -   X¹ may be a sulphur atom, —SO—, —SO₂— or —CH₂—;    -   R⁵ may be a C₁-C₄-alkyl or a C₁-C₄-halogenoalkyl having 1 to 5        halogen atoms; and    -   R⁹ and R¹⁰ may be the same or different and may be a hydrogen        atom or a C₁-C₄-alkyl.

A represents a heterocycle of the general formula (A-3)

-   -   in which:    -   R¹¹ may be a C₁-C₄-alkyl or a C₁-C₄-halogenoalkyl having 1 to 5        halogen atoms;

A represents a heterocycle of the general formula (A-4)

-   -   in which:    -   R¹² may be a C₁-C₄-alkyl or a C₁-C₄-halogenoalkyl having 1 to 5        halogen atoms.

A represents a heterocycle of the general formula (A-5)

-   -   in which:    -   R¹³ may be a hydrogen atom, a halogen atom, a C₁-C₄-alkyl or a        C₁-C₄-halogenoalkyl having 1 to 5 halogen atoms; and    -   R¹⁴ may be a halogen atom, a C₁-C₄-alkyl or a        C₁-C₄-halogenoalkyl having 1 to 5 halogen atoms.

A represents a heterocycle of the general formula (A-6)

-   -   in which:    -   R¹⁵ may be a hydrogen atom, a halogen atom, a C₁-C₄-alkyl or a        C₁-C₄-halogenoalkyl having 1 to 5 halogen atoms; and    -   R¹⁶ may be, a halogen atom, a C₁-C₄-alkyl or a        C₁-C₄-halogenoalkyl having 1 to 5 halogen atoms.

A represents a heterocycle of the general formula (A-7)

-   -   in which:    -   R¹⁷ and R¹⁹ may be the same or different and may be a hydrogen        atom, a halogen atom, a C₁-C₄-alkyl or a C₁-C₄-halogenoalkyl        having 1 to 5 halogen atoms; and    -   R¹⁸ may be a halogen atom, a C₁-C₄-alkyl or a        C₁-C₄-halogenoalkyl having 1 to 5 halogen atoms.

A represents a heterocycle of the general formula (A-8)

-   -   in which:    -   R²⁰ may be a hydrogen atom, a halogen atom, a C₁-C₄-alkyl or a        C₁-C₄-halogenoalkyl having 1 to 5 halogen atoms; and    -   R²¹ may be a halogen atom, a C₁-C₄-alkyl or a        C₁-C₄-halogenoalkyl having 1 to 5 halogen atoms.

A represents a heterocycle of the general formula (A-9)

-   -   in which:    -   R²² may be a hydrogen atom, a halogen atom, a C₁-C₄-alkyl or a        C₁-C₄-halogenoalkyl having 1 to 5 halogen atoms; and    -   R²³ may be, a halogen atom, a C₁-C₄-alkyl or a        C₁-C₄-halogenoalkyl having 1 to 5 halogen atoms

The present invention also relates to a process for the preparation ofthe compound of general formula (I). Thus, according to a further aspectof the present invention there is provided a process for the preparationof compound of general formula (I) as defined above, which comprisesreacting a heterocyclyl-ethylamine derivative of general formula (II) orone of its salt:

-   -   in which A, X, n, z, R¹, R², R³, R⁴ and R⁵ are as defined above;        with a carboxylic acid derivative of the general formula (III)

-   -   in which:    -   Y^(a), Y and p are as defined above; and

L′ is a leaving group chosen as being a halogen atom, a hydroxyl group,—OR²⁴, —OCOR²⁴, R²⁴ being a C₁-C₆ alkyl, a C₁-C₆ haloalkyl, a benzyl,4-methoxybenzyl, pentafluorophenyl, and a group of formula:

in the presence of a catalyst and, if L¹ is a hydroxyl group, in thepresence of a condensing agent.

The process according to the present invention is conducted in thepresence of a catalyst. Suitable catalyst may be chosen as being4-dimethyl-aminopyridine, 1-hydroxy-benzotriazole or dimethylformamide.

In case L¹ is a hydroxy group, the process according to the presentinvention is conducted in the presence of condensing agent. Suitablecondensing agent may be chosen as being acid halide former, such asphosgene, phosphorous tribromide, phosphorous trichloride, phosphorouspentachloride, phosphorous trichloride oxide or thionyl chloride;anhydride former, such as ethyl chloroformate, methyl chloroformate,isopropyl chloroformate, isobutyl chloroformate ormethanesulfonyl-chloride; carbodiimides, such asN,N′-dicyclohexylcarbodiimide (DCC) or other customary condensingagents, such as phosphorous pentoxide, polyphosphoric acid,N,N′-carbonyl-diimidazole,2-ethoxy-N-ethoxycarbonyl-1,2-dihydroquinoline (EEDQ),triphenylphosphine/tetrachloromethane,4-(4,6-dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloridehydrate or bromo-tripyrrolidino-phosphonium-hexafluorophosphate.

When R⁵ is a hydrogen atom, the above mentioned process for thepreparation of compound of general formula (I) may optionally becompleted by a further step according to the following reaction scheme:

-   -   in which:    -   A, X, n, z, R¹, R², R³, R⁴, Y^(a), Y and p are as defined above;    -   R^(5a) is a C₁-C₆-alkyl, or a C₃-C₇-cycloalkyl; and    -   L² is a leaving group chosen as being a halogen atom, a 4-methyl        phenylsulfonyloxy or a methylsulfonyloxy;        comprising the reaction of a compound of general formula (Ia)        with a compound of general formula (III) to provide a compound        of general formula (I).

Depending on the definition of R¹, R², R³, R⁴ or R⁵, amine derivativesof general formula (II) may be prepared by different processes. Oneexample (A) of such a process may be when:

-   -   A, z, X, n are as defined above; and    -   R¹ and R² are independently chosen as being a C₁-C₆ alkyl or a        C₃-C₇ cycloalkyl-C₁-C₆ alkyl    -   R³, R⁴ and R⁵ are hydrogen atoms;        then, the amine derivative of general formula (H) may be        prepared according to a process which comprises:

a first step according to reaction scheme A-1:

in which:

-   -   A, z, X and n are as defined above;    -   R²⁵ is a C₁-C₆ alkyl, a C₁-C₆ haloalkyl, a benzyl,        4-methoxybenzyl or pentafluorophenyl;    -   U is a leaving group chosen as being a halogen, a C₁-C₆        alkylsulfonate or a C₁-C₆ haloalkylsulfonate; comprising the        arylation of a cyanoacetate derivative of general formula (Va)        by a heterocylic derivative of general formula (IV), to provide        a heterocyclyl-cyanoacetate derivative of general formula (VI),        in the presence of a base, at a temperature of from 0° C. to        200° C.;

a second step according to reaction scheme A-2:

in which:

-   -   A, z, X and n are as defined above;    -   R²⁵ is a C₁-C₆ alkyl, a C₁-C₆ haloalkyl, a benzyl,        4-methoxybenzyl or pentafluorophenyl;        comprising a basic hydrolysis, an acidic hydrolysis or a        displacement by an halide of a compound of general formula (VI)        in the same or a different pot to provide, upon heating at a        temperature of from 40° C. to reflux, a        heterocylclyl-acetonitrile derivative of general formula (VIIa);

a third step according to reaction scheme A-3

in which:

-   -   A, z, X and n are as defined above;    -   R¹ is a C₁-C₆ alkyl or a C₃-C₇ cycloalkyl-C₁-C₆ alkyl,    -   W is a halogen atom, a C₁-C₆ alkylsulfonate, a C₁-C₆        haloalkylsulfonate or a 4-methyl-phenylsulfonate;        comprising the alkylation of a compound of general formula        (VII a) by a reagent of general formula (VIII a) to provide a        compound of general formula (VII b);

a fourth step according to reaction scheme A-4:

in which:

-   -   A, z, X and n are as defined above;    -   R¹, R² are a C₁-C₆ alkyl or a C₃-C₇ cycloalkyl-C₁-C₆ alkyl,    -   W is a halogen atom, a C₁-C₆ alkylsulfonate, a C₁-C₆        haloalkylsulfonate or a 4-methyl-phenylsulfonate;        comprising the alkylation of a compound of general formula        (VII b) by a reagent of general formula (VIIIb) to provide a        compound of general formula (VIIc);

a fifth step according to reaction scheme A-5

in which:

-   -   A, z, X and n are as defined above;    -   R¹, R² are a hydrogen atom, a C₁-C₆ alkyl or a C₃-C₇        cycloalkyl-C₁-C₆ alkyl,    -   L³ is a leaving group chosen as being a —OR²⁶ group or a —OCOR²⁶        group, R²⁶ being a C₁-C₆ alkyl, a C₁-C₆ haloalkyl, a benzyl,        4-methoxybenzyl or pentafluorophenyl;    -   PG represents a protecting group which may be a —COOR²⁷ group or        —COR²⁷ group, R²⁷ being a C₁-C₆ alkyl, a C₁-C₆ haloalkyl, a        benzyl, 4-methoxybenzyl or pentafluorophenyl;        comprising the reduction, by hydrogenation or by an hydride        donor, of a compound of general formula (VIIa), (VIIb) or        (VIIc), in the presence of a catalyst and in the presence of a        compound of general formula (IX) to produce a compound of        general formula (X), at a temperature of from 0° C. to 150° C.        and under a pressure of from 1 bar and 100 bar,

a sixth step according to reaction scheme A-6:

in which:

-   -   A, z, X and n are as defined above;    -   R¹, R² are a hydrogen atom, a C₁-C₆ alkyl or a C₃-C₇        cycloalkyl-C₁-C₆ alkyl,    -   PG represents a protecting group which may be a —COOR²⁸ group or        —COR²⁸ group, R²⁸ being a C₁-C₆ alkyl, a C₁-C₆ haloalkyl, a        benzyl, 4-methoxybenzyl or pentafluorophenyl;        comprising a deprotection reaction, in an acidic or in a basic        medium, of a compound of general formula (X) to provide an amine        derivative of general formula (II) or one of its salt.

The first step (step A-1) is conducted in the presence of a base.Preferably, the base will be chosen as being an inorganic or an organicbase. Suitable examples of such bases may for example be alkaline earthmetal or alkali metal hydrides, hydroxides, amides, alcoholates,carbonates or hydrogen carbonates, acetates or tertiary amines.

The first step (step A-1) according to the present invention isconducted at a temperature of from 0° C. to 200° C. Preferably, firststep (step A-1) is conducted at a temperature of from 0° C. to 120° C.,more preferably at a temperature of from 0° C. to 80° C.

The first step (step A-1) according to the present invention may beconducted in the presence of a solvent. Preferably, the solvent ischosen as being water, an organic solvent or a mixture of both. Suitableorganic solvents may for example be aliphatic, alicyclic or aromaticsolvent.

The first step (step A-1) according to the present invention may also beconducted in the presence of a catalyst. Preferably, the catalyst ischosen as being palladium salts or complexes. More preferably, thecatalyst is chosen as being a palladium complex. Suitable palladiumcomplex catalyst may for example be generated directly in the reactionmixture by separately adding to the reaction mixture a palladium saltand a complex ligand. Suitable ligands may for example be bulkyphosphines or arsines ligands, such as(R)-(−)-1-[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyldicyclohexylphosphineand its corresponding enantiomer, or a mixture of both;(R)-(−)-1[(S)-2-(dicyclohexylphosphino)ferrocenyl]ethyldiphenylphosphineand its corresponding enantiomer, or a mixture of both;(R)-(−)-1[(S)-2-(diphenylphosphino)ferrocenyl]ethyldi-t-butylphosphineand its corresponding enantiomer, or a mixture of both; or(R)-(−)-1[(S)-2-(diphenylphosphino)ferrocenyl]ethyldicyclohexylphosphineand its corresponding enantiomer, or a mixture of both.

The fifth step (step A-5) according to the present invention isconducted in the presence of a hydride donor. Preferably, the hydridedonor is chosen as being metal or metalloid hydrides such as LiAlH₄,NaBH₄, KBH₄, B₂H₆.

The fifth step (step A-5) according to the present invention isconducted in the presence of a catalyst. Preferably, the catalyst ischosen as being Co(II)-Chloride, Ni(II)-chloride, ammonia or one of itssalt, Palladium on charcoal, Raney Nickel, Raney Cobalt or Platinum.

The fifth step (step A-5)) according to the present invention isconducted at a temperature of from 0° C. to 150° C. Preferably thetemperature is of from 10° C. to 120° C. More preferably, thetemperature is of from 10° C. to 80° C.

The fifth step (step A-5) according to the present invention isconducted under a pressure of from 1 bar to 100 bar. Preferably thepressure is of from 1 bar to 50 bar.

The fifth step (step A-5) according to the present invention may beconducted in the presence of an organic solvent, of water or of amixture thereof. Preferably, the solvent is chosen as being ether,alcohol, carboxylic acid, or a mixture thereof with water or pure water.

The compound according to the present invention can be preparedaccording to the general processes of preparation described above. Itwill nevertheless be understood that, on the basis of his generalknowledge and of available publications, the skilled worker will be ableto adapt this method according to the specifics of each of thecompounds, which it is desired to synthesise.

On the basis of his general knowledge and of available publications, theskilled worker will also be able to prepare intermediate compound offormula (V) according to the present invention.

The present invention also relates to a fungicidal compositioncomprising an effective amount of an active material of general formula(I). Thus, according to the present invention, there is provided afungicidal composition comprising, as an active ingredient, an effectiveamount of a compound of general formula (I) as defined above and anagriculturally acceptable support, carrier or filler.

In the present specification, the term “support” denotes a natural orsynthetic, organic or inorganic material with which the active materialis combined to make it easier to apply, notably to the parts of theplant. This support is thus generally inert and should be agriculturallyacceptable. The support may be a solid or a liquid. Examples of suitablesupports include clays, natural or synthetic silicates, silica, resins,waxes, solid fertilisers, water, alcohols, in particular butanol,organic solvents, mineral and plant oils and derivatives thereof.Mixtures of such supports may also be used.

The composition may also comprise additional components. In particular,the composition may further comprise a surfactant. The surfactant can bean emulsifier, a dispersing agent or a wetting agent of ionic ornon-ionic type or a mixture of such surfactants. Mention may be made,for example, of polyacrylic acid salts, lignosulphonic acid salts,phenolsulphonic or naphthalenesulphonic acid salts, polycondensates ofethylene oxide with fatty alcohols or with fatty acids or with fattyamines, substituted phenols (in particular alkylphenols or arylphenols),salts of sulphosuccinic acid esters, taurine derivatives (in particularalkyl taurates), phosphoric esters of polyoxyethylated alcohols orphenols, fatty acid esters of polyols, and derivatives of the abovecompounds containing sulphate, sulphonate and phosphate functions. Thepresence of at least one surfactant is generally essential when theactive material and/or the inert support are water-insoluble and whenthe vector agent for the application is water. Preferably, surfactantcontent may be comprised between 5% and 40% by weight of thecomposition.

Optionally, additional components may also be included, e.g. protectivecolloids, adhesives, thickeners, thixotropic agents, penetration agents,stabilisers, sequestering agents. More generally, the active materialscan be combined with any solid or liquid additive, which complies withthe usual formulation techniques.

In general, the composition according to the invention may contain from0.05 to 99% (by weight) of active material, preferably 10 to 70% byweight.

Compositions according to the present invention can be used in variousforms such as aerosol dispenser, capsule suspension, cold foggingconcentrate, dustable powder, emulsifiable concentrate, emulsion oil inwater, emulsion water in oil, encapsulated granule, fine granule,flowable concentrate for seed treatment, gas (under pressure), gasgenerating product, granule, hot fogging concentrate, macrogranule,microgranule, oil dispersible powder, oil miscible flowable concentrate,oil miscible liquid, paste, plant rodlet, powder for dry seed treatment,seed coated with a pesticide, soluble concentrate, soluble powder,solution for seed treatment, suspension concentrate (flowableconcentrate), ultra low volume (ulv) liquid, ultra low volume (ulv)suspension, water dispersible granules or tablets, water dispersiblepowder for slurry treatment, water soluble granules or tablets, watersoluble powder for seed treatment and wettable powder.

These compositions include not only compositions which are ready to beapplied to the plant or seed to be treated by means of a suitabledevice, such as a spraying or dusting device, but also concentratedcommercial compositions which must be diluted before application to thecrop.

The compounds of the invention can also be mixed with one or moreinsecticides, fungicides, bactericides, attractant acaricides orpheromones or other compounds with biological activity. The mixturesthus obtained have a broadened spectrum of activity. The mixtures withother fungicides are particularly advantageous. Examples of suitablefungicide mixing partners may be selected in the following lists:

1) a compound capable to inhibit the nucleic acid synthesis likebenalaxyl, benalaxyl-M, bupirimate, chiralaxyl, clozylacon,dimethirimol, ethirimol, furalaxyl, hymexazol, mefenoxam, metalaxyl,metalaxyl-M, ofurace, oxadixyl, oxolinic acid;

2) a compound capable to inhibit the mitosis and cell division likebenomyl, carbendazim, diethofencarb, ethaboxam, fuberidazole,pencycuron, thiabendazole thiophanate-methyl, zoxamide;

3) a compound capable to inhibit the respiration for example

as CI-respiration inhibitor like diflumetorim;

as CII-respiration inhibitor like boscalid, carboxin, fenfuram,flutolanil, furametpyr, furmecyclox, mepronil, oxycarboxine,penthiopyrad, thifluzamide;

as CIII-respiration inhibitor like amisulbrom, azoxystrobin, cyazofamid,dimoxystrobin, enestrobin, famoxadone, fenamidone, fluoxastrobin,kresoxim-methyl, metominostrobin, orysastrobin, picoxystrobin,pyraclostrobin, trifloxystrobin;

4) a compound capable of to act as an uncoupler like dinocap, fluazinam,meptyldinocap;

5) a compound capable to inhibit ATP production like fentin acetate,fentin chloride, fentin hydroxide, silthiofam;

6) a compound capable to inhibit AA and protein biosynthesis likeandoprim, blasticidin-S, cyprodinil, kasugamycin, kasugamycinhydrochloride hydrate, mepanipyrim, pyrimethanil;

7) a compound capable to inhibit the signal transduction likefenpiclonil, fludioxonil, quinoxyfen;

8) a compound capable to inhibit lipid and membrane synthesis likebiphenyl, chlozolinate, edifenphos, iodocarb, iprobenfos, iprodione,isoprothiolane, procymidone, propamocarb, propamocarb hydrochloride,pyrazophos, tolclofos-methyl, vinclozolin;

9) a compound capable to inhibit ergosterol biosynthesis like aldimorph,azaconazole, bitertanol, bromuconazole, cyproconazole, diclobutrazole,difenoconazole, diniconazole, diniconazole-M, dodemorph, dodemorphacetate, epoxiconazole, etaconazole, fenarimol, fenbuconazole,fenhexamid, fenpropidin, fenpropimorph, fluquinconazole, flurprimidol,flusilazole, flutriafol, furconazole, furconazole-cis, hexaconazole,imazalil, imazalil sulfate, imibenconazole, ipconazole, metconazole,myclobutanil, naftifine, nuarimol, oxpoconazole, paclobutrazol,pefurazoate, penconazole, prochloraz, propiconazole, prothioconazole,pyributicarb, pyrifenox, simeconazole, spiroxamine, tebuconazole,terbinafine, tetraconazole, triadimefon, triadimenol, tridemorph,triflumizole, triforine, triticonazole, uniconazole, viniconazole,voriconazole;

10) a compound capable to inhibit cell wall synthesis likebenthiavalicarb, bialaphos, dimethomorph, flumorph, iprovalicarb,polyoxins, polyoxorim, validamycin A;

11) a compound capable to inhibit melanine biosynthesis likecarpropamid, diclocymet, fenoxanil, phthalide, pyroquilon, tricyclazole;

12) a compound capable to induce a host defence likeacibenzolar-S-methyl, probenazole, tiadinil;

13) a compound capable to have a multisite action like Bordeaux mixture,captafol, captan, chlorothalonil, copper naphthenate, copper oxide,copper oxychloride, copper preparations such as copper hydroxide, coppersulphate, dichlofluanid, dithianon, dodine, dodine free base, ferbam,fluorofolpet, folpet, guazatine, guazatine acetate, iminoctadine,iminoctadine albesilate, iminoctadine triacetate, mancopper, mancozeb,maneb, metiram, metiram zinc, oxine-copper, propineb, sulphur andsulphur preparations including calcium polysulphide, thiram,tolylfluanid, zineb, ziram;

14) a compound selected in the following list:(2E)-2-(2-{[6-(3-chloro-2-methylphenoxy)-5-fluoropyrimidin-4-yl]oxy}phenyl)-2-(methoxyimino)-N-methylacetamide,(2E)-2-{2-[({[(1E)-1-(3-{[(E)-1-fluoro-2-phenylvinyl]oxy}phenyl)ethylidene]amino}oxy)methyl]phenyl}-2-(methoxyimino)-N-methylacetamide,1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)cycloheptanol,1-[(4-methoxyphenoxy)methyl]-2,2-dimethylpropyl1H-imidazole-1-carboxylate,2-(4-chlorophenyl)-N-{2-[3-methoxy-4-(prop-2-yn-1-yloxy)phenyl]ethyl}-2-(prop-2-yn-1-yloxy)acetamide,2,3,5,6-tetrachloro-4-(methylsulfonyl)pyridine,2-butoxy-6-iodo-3-propyl-4H-chromen-4-one,2-chloro-N-(1,1,3-trimethyl-2,3-dihydro-1H-inden-4-yl)nicotinamide,2-phenylphenol and salts, 3,4,5-trichloropyridine-2,6-dicarbonitrile,3,4-dichloro-N-(2-cyanophenyl)isothiazole-5-carboxamide,3-[5-(4-chlorophenyl)-2,3-dimethylisoxazolidin-3-yl]pyridine,5-chloro-6-(2,4,6-trifluorophenyl)-N-[(1R)-1,2,2-trimethylpropyl][1,2,4]triazolo[1,5-a]pyrimidin-7-amine,5-chloro-7-(4-methylpiperidin-1-yl)-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]pyrimidine,5-chloro-N-[(1R)-1,2-dimethylpropyl]-6-(2,4,6-trifluorophenyl)[1,2,4]triazolo[1,5-a]pyrimidin-7-amine,8-hydroxyquinoline sulfate, benthiazole, bethoxazin, capsimycin,carvone, chinomethionat, cufraneb, cyflufenamid, cymoxanil, dazomet,debacarb, dichlorophen, diclomezine, dicloran, difenzoquat, difenzoquatmethylsulphate, diphenylamine, ferimzone, flumetover, fluopicolide,fluoroimide, flusulfamide, fosetyl-aluminium, fosetyl-calcium,fosetyl-sodium, hexachlorobenzene, irumamycin, methasulfocarb, methyl(2-chloro-5-{(1E)-N-[(6-methylpyridin-2-yl)methoxy]ethanimidoyl}benzyl)carbamate,methyl(2E)-2-{2-[({cyclopropyl[(4-methoxyphenyl)imino]methyl}thio)methyl]phenyl}-3-methoxyacrylate,methyl1-(2,2-dimethyl-2,3-dihydro-1H-inden-1-yl)-1H-imidazole-5-carboxylate,methyl3-(4-chlorophenyl)-3-{[N-(isopropoxycarbonyl)valyl]amino}propanoate,methyl isothiocyanate, metrafenone, mildiomycin,N-(3′,4′-dichloro-5-fluorobiphenyl-2-yl)-3-(difluoromethyl)-1-methyl-1H-pyrazole-4-carboxamide,N-(3-ethyl-3,5,5-trimethylcyclohexyl)-3-(formylamino)-2-hydroxybenzamide,N-(4-chloro-2-nitrophenyl)-N-ethyl-4-methylbenzenesulfonamide,N-[(5-bromo-3-chloropyridin-2-yl)methyl]-2,4-dichloronicotinamide,N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2,4-dichloronicotinamide,N-[1-(5-bromo-3-chloropyridin-2-yl)ethyl]-2-fluoro-4-iodonicotinamide,N-[2-(4-{[3-(4-chlorophenyl)prop-2-yn-1-yl]oxy}-3-methoxyphenyl)ethyl]-N<sup>2</sup>-(methylsulfonyl)valinamide,N-{(Z)-[(cyclopropylmethoxy)imino][6-(difluoromethoxy)-2,3-difluorophenyl]methy}-2-phenylacetamide,N-{2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]ethyl}-2-(trifluoromethyl)benzamide,natamycin, nickel dimethyldithiocarbamate, nitrothal-isopropyl,O-{1-[(4-methoxyphenoxy)methyl]-2,2-dimethylpropyl}1H-imidazole-1-carbothioate,octhilinone, oxamocarb, oxyfenthiin, pentachlorophenol and salts,phosphorous acid and its salts, piperalin, propamocarb fosetylate,propanosine-sodium, proquinazid, pyrrolnitrine, quintozene, tecloftalam,tecnazene, triazoxide, trichlamide and zarilamid.

The composition according to the invention comprising a mixture of acompound of formula (I) with a bactericide compound may also beparticularly advantageous. Examples of suitable bactericide mixingpartners may be selected in the following list: bronopol, dichlorophen,nitrapyrin, nickel dimethyldithiocarbamate, kasugamycin, octhilinone,furancarboxylic acid, oxytetracycline, probenazole, streptomycin,tecloftalam, copper sulphate and other copper preparations.

The fungicidal compositions of the present invention can be used tocuratively or preventively control the phytopathogenic fungi of crops.Thus, according to a further aspect of the present invention, there isprovided a method for curatively or preventively controlling thephytopathogenic fingi of crops characterised in that a fungicidalcomposition as hereinbefore defined is applied to the seed, the plantand/or to the fruit of the plant or to the soil in which the plant isgrowing or in which it is desired to grow.

The composition as used against phytopathogenic fungi of crops comprisesan effective and non-phytotoxic amount of an active material of generalformula (I).

The expression “effective and non-phytotoxic amount” means an amount ofcomposition according to the invention which is sufficient to control ordestroy the fungi present or liable to appear on the crops, and whichdoes not entail any appreciable symptom of phytotoxicity for the saidcrops. Such an amount can vary within a wide range depending on thefungus to be controlled, the type of crop, the climatic conditions andthe compounds included in the fungicidal composition according to theinvention.

This amount can be determined by systematic field trials, which arewithin the capabilities of a person skilled in the art.

The method of treatment according to the present invention is useful totreat propagation material such as tubers or rhizomes, but also seeds,seedlings or seedlings pricking out and plants or plants pricking out.This method of treatment can also be useful to treat roots. The methodof treatment according to the present invention can also be useful totreat the overground parts of the plant such as trunks, stems or stalks,leaves, flowers and fruits of the concerned plant.

Among the plants that can be protected by the method according to thepresent invention, mention may be made of cotton; flax; vine; fruit orvegetable crops such as Rosaceae sp. (for instance pip fruit such asapples and pears, but also stone fruit such as apricots, almonds andpeaches), Ribesioidae sp., Juglandaceae sp., Betulaceae sp.,Anacardiaceae sp., Fagaceae sp., Moraceae sp., Oleaceae sp.,Actinidaceae sp., Lauraceae sp., Musaceae sp. (for instance banana treesand plantins), Rubiaceae sp., Theaceae sp., Sterculiceae sp., Rutaceaesp. (for instance lemons, oranges and grapefruit); Solanaceae sp. (forinstance tomatoes), Liliaceae sp., Asteraceae sp. (for instancelettuces), Umbelliferae sp., Cruciferae sp., Chenopodiaceae sp.,Cucurbitaceae sp., Papilionaceae sp. (for instance peas), Rosaceae sp.(for instance strawberries); major crops such as Graminae sp. (forinstance maize, lawn or cereals such as wheat, rice, barley andtriticale), Asteraceae sp. (for instance sunflower), Cruciferae sp. (forinstance colza), Fabacae sp. (for instance peanuts), Papilionaceae sp.(for instance soybean), Solanaceae sp. (for instance potatoes),Chenopodiaceae sp. (for instance beetroots); horticultural and forestcrops; as well as genetically modified homologues of these crops.

Among the diseases of plants or crops that can be controlled by themethod according to the present invention, mention may be made of:

Powdery mildew diseases such as:

Blumeria diseases, caused for example by Blumeria graminis;

Podosphaera diseases, caused for example by Podosphaera leucotricha;

Sphaerotheca diseases, caused for example by Sphaerotheca fuliginea;

Uncinula diseases, caused for example by Uncinula necator;

Rust diseases such as:

Gymnosporangium diseases, caused for example by Gymnosporangium sabinae;

Hemileia diseases, caused for example by Hemileia vastatrix;

Phakopsora diseases, caused for example by Phakopsora pachyrhizi orPhakopsora meibomiae;

Puccinia diseases, caused for example by Puccinia recondita;

Uromyces diseases, caused for example by Uromyces appendiculatus;Oomycete diseases such as:

Bremia diseases, caused for example by Bremia lactucae;

Peronospora diseases, caused for example by Peronospora pisi or P.brassicae;

Phytophthora diseases, caused for example by Phytophthora infestans;

Plasmopara diseases, caused for example by Plasmopara viticola;

Pseudoperonospora diseases, caused for example by Pseudoperonosporahumuli or

Pseudoperonospora cubensis;

Pythium diseases, caused for example by Pythium ultimum;

Leafspot, leaf blotch and leaf blight diseases such as:

Alternaria diseases, caused for example by Alternaria solani;

Cercospora diseases, caused for example by Cercospora beticola;

Cladiosporum diseases, caused for example by Cladiosporium cucumerinum;

Cochliobolus diseases, caused for example by Cochliobolus sativus;

Colletotrichum diseases, caused for example by Colletotrichumlindemuthanium;

Cycloconium diseases, caused for example by Cycloconium oleaginum;

Diaporthe diseases, caused for example by Diaporthe citri;

Elsinoe diseases, caused for example by Elsinoe fawcettii;

Gloeosporium diseases, caused for example by Gloeosporium laeticolor,

Glomerella diseases, caused for example by Glomerella cingulata;

Guignardia diseases, caused for example by Guignardia bidwelli;

Leptosphaeria diseases, caused for example by Leptosphaeria maculans;Leptosphaeria nodorum;

Magnaporthe diseases, caused for example by Magnaporthe grisea;

Mycosphaerella diseases, caused for example by Mycosphaerellagraminicola; Mycosphaerella arachidicola; Mycosphaerella fijiensis;

Phaeosphaeria diseases, caused for example by Phaeosphaeria nodorum;

Pyrenophora diseases, caused for example by Pyrenophora teres;

Ramularia diseases, caused for example by Ramularia collo-cygni;

Rhynchosporium diseases, caused for example by Rhynchosporium secalis;

Septoria diseases, caused for example by Septoria apii or Septorialycopercisi;

Typhula diseases, caused for example by Typhula incarnata;

Venturia diseases, caused for example by Venturia inaequalis;

Root and stem diseases such as:

Corticium diseases, caused for example by Corticium graminearum;

Fusarium diseases, caused for example by Fusarium oxysporum;

Gaeumannomyces diseases, caused for example by Gaeumannomyces graminis;

Rhizoctonia diseases, caused for example by Rhizoctonia solani;

Tapesia diseases, caused for example by Tapesia acuformis;

Thielaviopsis diseases, caused for example by Thielaviopsis basicola;

Ear and panicle diseases such as:

Alternaria diseases, caused for example by Alternaria spp.;

Aspergillus diseases, caused for example by Aspergillus flavus;

Cladosporium diseases, caused for example by Cladosporium spp.;

Claviceps diseases, caused for example by Claviceps purpurea;

Fusarium diseases, caused for example by Fusarium culmorum;

Gibberella diseases, caused for example by Gibberella zeae;

Monographella diseases, caused for example by Monographella nivalis;

Smut and bunt diseases such as:

Sphacelotheca diseases, caused for example by Sphacelotheca reiliana;

Tilletia diseases, caused for example by Tilletia caries;

Urocystis diseases, caused for example by Urocystis occulta;

Ustilago diseases, caused for example by Ustilago nuda;

Fruit rot and mould diseases such as:

Aspergillus diseases, caused for example by Aspergillus flavus;

Botrytis diseases, caused for example by Botrytis cinerea;

Penicillium diseases, caused for example by Penicillium expansum;

Sclerotinia diseases, caused for example by Sclerotinia sclerotiorum;

Verticilium diseases, caused for example by Verticilium alboatrum;

Seed and soilborne decay, mould, wilt, rot and damping-off diseases:

Fusarium diseases, caused for example by Fusarium culmorum;

Phytophthora diseases, caused for example by Phytophthora cactorum;

Pythium diseases, caused for example by Pythium ultimum;

Rhizoctonia diseases, caused for example by Rhizoctonia solani;

Sclerotium diseases, caused for example by Sclerotium rolfsii;

Microdochium diseases, caused for example by Microdochium nivale;

Canker, broom and dieback diseases such as:

Nectria diseases, caused for example by Nectria galligena;

Blight diseases such as:

Monilinia diseases, caused for example by Monilinia laxa;

Leaf blister or leaf curl diseases such as:

Taphrina diseases, caused for example by Taphrina deformans;

Decline diseases of wooden plants such as:

Esca diseases, caused for example by Phaemoniella clamydospora;

Diseases of flowers and Seeds such as:

Botrytis diseases, caused for example by Botrytis cinerea;

Diseases of tubers such as:

Rhizoctonia diseases, caused for example by Rhizoctonia solani.

The fungicide composition according to the present invention may also beused against fungal diseases liable to grow on or inside timber. Theterm “timber” means all types of species of wood, and all types ofworking of this wood intended for construction, for example solid wood,high-density wood, laminated wood, and plywood. The method for treatingtimber according to the invention mainly consists in contacting one ormore compounds of the present invention, or a composition according tothe invention; this includes for example direct application, spraying,dipping, injection or any other suitable means.

The dose of active material usually applied in the treatment accordingto the present invention is generally and advantageously between 10 and800 g/ha, preferably between 50 and 300 g/ha for applications in foliartreatment. The dose of active substance applied is generally andadvantageously between 2 and 200 g per 100 kg of seed, preferablybetween 3 and 150 g per 100 kg of seed in the case of seed treatment. Itis clearly understood that the doses indicated above are given asillustrative examples of the invention. A person skilled in the art willknow how to adapt the application doses according to the nature of thecrop to be treated.

The fungicidal composition according to the present invention may alsobe used in the treatment of genetically modified organisms with thecompounds according to the invention or the agrochemical compositionsaccording to the invention. Genetically modified plants are plants intowhose genome a heterologous gene encoding a protein of interest has beenstably integrated. The expression “heterologous gene encoding a proteinof interest” essentially means genes which give the transformed plantnew agronomic properties, or genes for improving the agronomic qualityof the transformed plant.

The compositions according to the present invention may also be used forthe preparation of composition useful to curatively or preventivelytreat human and animal fungal diseases such as, for example, mycoses,dermatoses, trichophyton diseases and candidiases or diseases caused byAspergillus spp., for example Aspergillus fumigatus.

The aspects of the present invention will now be illustrated withreference to the following tables of compounds and examples. Thefollowing Table illustrates in a non-limiting manner examples offungicidal compounds according to the present invention. In thefollowing Examples, M+1 (or M−1) means the molecular ion peak, plus orminus 1 a.m.u. (atomic mass units) respectively, as observed in massspectroscopy and M (ApcI+) means the molecular ion peak as it was foundvia positive atmospheric pressure chemical ionisation in massspectroscopy.

TABLE A

Compound X¹ X² X³ Y^(a) Y¹ Y² Y³ Y⁴ R¹ R² R³ R⁴ R⁵ M + 1 A-1 H Br H CF₃H H H H H H H H H 374

TABLE B

Compound X¹ X² X³ Y^(a) Y¹ Y² Y³ Y⁴ R¹ R² R³ R⁴ R⁵ M + 1 B-1 H H Cl CF₃H H H H H H H H H 330

TABLE C

Compound X¹ X² X³ Y^(a) Y¹ Y² Y³ Y⁴ R¹ R² R³ R⁴ R⁵ M + 1 C-1 H H Cl CF₃H H H H H H H H H 330

EXAMPLES OF PROCESS FOR THE PREPARATION OF THE COMPOUND OF GENERALFORMULA (I) Synthesis ofN-[2-(5-bromopyrimidin-2-yl)ethyl]-2-(trifluoromethyl)benzamide(Compound A-1) Synthesis of ethyl (5-bromopyrimidin-2-yl)(cyano)acetate

To a chilled stirred suspension of sodium hydride (60% in oil, 34.55mmol) in tetrahydrofuran (20 mL) was added 1.17 g of ethyl cyanoacetate(10.34 mmol) portionwise over 10 minutes. After effervescence hasceased, the yellow cloudy mixture was left to warm up to roomtemperature whilst stirring. 2.00 g of 5-bromo,2-bromo-pyrimidine (10.34mmol) in 30 mL of tetrahydrofuran was added. And the mixture was left tostir at room temperature for six hours. The resultant brown mixture wasconcentrated under reduced pressure to give a bright brown precipitateto which water (200 mL) was added. After extraction with heptane (200mL), the aqueous phase was acidified by the addition of HCl 1M and theresultant precipitate was collected by filtration to give on dryingethyl (5-bromopyrimidin-2-yl)(cyano)acetate as a bright brown powder(0.67 g, yield=24%).

¹H NMR δ (ppm, DMSO-d₆): 3.5 (b, 1H); 8.9 (b, 1H); 8.45 (b, 1H); 4.24(t, 2H); 1.25 (t, 3H).

Synthesis of (5-bromopyrimidin-2-yl)acetonitrile

To 2.70 g of ethyl (5-bromopyrimidin-2-yl)(cyano)acetate (9.970 mmol) indimethylsulfoxyde (20 ml) was added 0.584 g of sodium chloride (9.970mmol) and 0.18 mL of water (9.970 mmol). The mixture was heated at 120°C. under a nitrogen atmosphere for 3 hours. The mixture was poured intowater (300 mL) and the resultant precipitate was collected by filtrationto give 5-bromopyrimidin-2-yl)acetonitrile (0.6 g, yield=30%).

The clear yellow filtrate was salted by the addition of a saturatedsolution of sodium chloride, neutralided with sodium hydroxide, to givea red solution which was then extracted with dichloromethane. Theorganic phase was collected, dried over magnesium sulphate, andevaporated in vacuo to give a dark oil, which was purified by flashchromatography using 2/1 heptane/ethyl acetate as eluent, yielding to5-bromopyrimidin-2-yl)acetonitrile (0.9 g, yield=43%).

¹H NMR δ (ppm, CDCl₃): 9.0 (s, 2H); 4.25 (s, 2H).

Synthesis of tert-butyl [2-(5-bromopyrimidin-2-yl)ethyl]carbamate

To a cold (−5° C. to 0° C.), stirred mixture of the5-bromopyrimidin-2-yl)acetonitrile (0.9 g), tert-butyloxy-carbonate(1.98 g; 2 equivalents), and nickel chloride hexahydrate (1.08 g) undera nitrogen atmosphere was added, portionwise, sodium borohydride (0.86g; 5 equivalents). After the addition the mixture was left to stir,whilst warming to room temperature, for 6 hrs and left to standovernight.

The mixture was diluted with ethyl acetate (200 mls) and filteredthrough kieselghur. The filtrate was washed with brine and the organicphase was collected, dried over MgSO₄, and evaporated in vacuo to givethe product as a brown oil. Yield: 0.6 g

The crude product was purified by flash chromatography to yield to 0.22g of tert-butyl [2-(5-bromopyrimidin-2-yl)ethyl]carbamate (16%)

¹H NMR δ (CDCl₃): 8.76 (s, 2H); 5.22 (b, NH); 3.64 (m, 2H); 3.13 (m,2H); 1.43 (s, 9H).

Synthesis ofN-[2-(5-bromopyrimidin-2-yl)ethyl]-2-(trifluoromethyl)benzamide(Compound 1)

To a clear pale yellow mixture of the tert-butyl[2-(5-bromopyrimidin-2-yl)ethyl]carbamate (0.22 g, 0.7 mmol) indichloromethane (2 ml) was added trifluoroacetic acid (10 equivs) andthe mixture was left to stir at room temperature for 7 hrs and left tostand overnight. Saturated sodium bicarbonate solution was added untilthe effervescence stopped (to give a basic medium). The organic phasewas collected, dried over MgSO4, and evaporated in vacuo afterfiltration, to yield to 0.12 g of 2-(5-bromopyrimidin-2-yl)ethanamine(80%) which is used directly without purification.

To 0.06 g of 2-(5-bromopyrimidin-2-yl)ethanamine (3.0 mmol) andtriethylamine (0.03 g, 1.0 equivalent) in THF (5 ml), at roomtemperature whilst stirring, was added the 2-trifluoromethyl benzoylchloride (0.062 g, 1.0 equivalent) and the mixture was left to stir atroom temperature overnight. The solvent was removed by evaporation invacuo and saturated sodium bicarbonate (10 mls) was added. The mixturewas extracted with dichloromethane and the organic phase was collected,dried over MgSO₄, and evaporated in vacuo to give the crude productwhich was purified by chromatography on silica using 1:1 heptane/ethylacetate to yield to 0.036 g ofN-[2-(5-bromopyrimidin-2-yl)ethyl]-2-(trifluoromethyl)benzamide(Compound A-1) (32%).

¹H NMR 5 (ppm, CDCl₃): 8.72 (s, 2H); 8.74-8.57 (m, 4H); 6.72 (b, NH);3.94 (q, 2H); 2.28 (m, 2H).

Mass Spectrum: [M+I]=374.

EXAMPLES OF BIOLOGICAL ACTIVITY OF THE COMPOUND OF GENERAL FORMULA (I)Example A In Vivo Test on Alternaria brassicae (Leaf Spot of Crucifers)

The active ingredient tested is prepared by potter homogenisation in aconcentrated suspension type formulation at 100 g/l. This suspension isthen diluted with water to obtain the desired active materialconcentration.

Radish plants (Pernot variety) in starter cups, sown on a 50/50 peatsoil-pozzolana substrate and grown at 18-20° C., are treated at thecotyledon stage by spraying with the aqueous suspension described above.

Plants, used as controls, are treated with an aqueous solution notcontaining the active material.

After 24 hours, the plants are contaminated by spraying them with anaqueous suspension of Alternaria brassicae spores (40,000 spores percm³). The spores are collected from a 12-13-day-old culture.

The contaminated radish plants are incubated for 6-7 days at about 18°C., under a humid atmosphere.

Grading is carried out 6 to 7 days after the contamination, incomparison with the control plants.

Under these conditions, good (at least 50%) is observed at a dose of 500ppm with the compounds: A1.

TheN-{1-methylcarbamoyl-2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]-ethyl}-4-phenylbenzamidedisclosed by Patent Application WO 01/11965 (see compound 316 in TableD) showed poor effectiveness on Alternaria brassicae, and zeroeffectiveness on Botrytis cinerea at 330 ppm; theN-{1-ethylcarbamoyl-2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl}-3-nitrobenzamidealso disclosed by Patent Application WO 01/11965 (see compound 307 inTable D) showed poor effectiveness on Alternaria brassicae and zeroeffectiveness on Botrytis cinerea at 330 ppm; theN-{1-ethylcarbamoyl-2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]-ethyl}-benzamideand theN-{1-methylcarbamoyl-2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl}-benzamidealso disclosed by Patent Application WO 01/11965 (see compounds 304 and314 in Table D) showed zero effectiveness on Botrytis cinerea at 330ppm; and theN-{1-ethylcarbamoyl-2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl}-4-chlorobenzamide,theN-{1-ethylcarbamoyl-2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl}-2-bromobenzamideand theN-{1-methylcarbamoyl-2-[3-chloro-5-(trifluoromethyl)-2-pyridinyl]ethyl}-4-methoxybenzamidealso disclosed by Patent Application WO 01/11965 (see compounds 306, 310and 315 in Table D) showed zero effectiveness on Botrytis cinerea at 330ppm.

TheN-{[3-chloro-5-(trifluoromethyl)-2-pyridinyl]methyl}-5-thienylacetamidedisclosed by Patent Application WO 01/11965 (see compound 101 in tableB) showed poor efficacy against Alternaria brassicae and no efficacyagainst Botrytis cinerea and Peronospora parasitica at 330 ppm.

1. A compound of general formula (I)

in which: n is 1, 2, or 3; p is 1, 2, 3 or 4; A is a pyrimidine ring; zis a carbon atom which can not be substituted by X; each X isindependently selected from the group consisting of a halogen atom, anitro group, a cyano group, a hydroxy group, an amino group, a sulfanylgroup, a pentafluoro-λ⁶-sulfanyl group, a formyl group, a formyloxygroup, a formylamino group, a carboxy group, a carbamoyl group, aN-hydroxycarbamoyl group, a carbamate group, a(hydroxyimino)-C₁-C₆-alkyl group, a C₁-C₈-alkyl, a C₂-C₈-alkenyl, aC₂-C₈-alkynyl, a C₁-C₈-alkylamino, a C₁-C₈-halogenoalkyl having 1 to 5halogen atoms, a di-C₁-C₈-alkylamino, a C₁-C₈-alkoxy, aC₁-C₈-halogenoalkoxy having 1 to 5 halogen atoms, a C₁-C₈-alkylsulfanyl,a C₁-C₈-halogenoalkylsulfanyl having 1 to 5 halogen atoms, aC₂-C₈-alkenyloxy, a C₂-C₈-halogenoalkenyloxy having 1 to 5 halogenatoms, a C₃-C₈-alkynyloxy, a C₃-C₈-halogenoalkynyloxy having 1 to 5halogen atoms, a C₃-C₈-cycloalkyl, a C₃-C₈-halogenocycloalkyl having 1to 5 halogen atoms, a C₁-C₈-alkylcarbonyl, a C₁-C₈-halogenoalkylcarbonylhaving 1 to 5 halogen atoms, a C₁-C₈-alkylcarbamoyl, adi-C₁-C₈-alkylcarbamoyl, a N—C₁-C₈-alkyloxycarbamoyl, aC₁-C₈-alkoxycarbamoyl, a N—C₁-C₈-alkyl-C₁-C₈-alkoxycarbamoyl, aC₁-C₈-alkoxycarbonyl, a C₁-C₈-halogenoalkoxycarbonyl having 1 to 5halogen atoms, a C₁-C₈-alkylcarbonyloxy, aC₁-C₈-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, aC₁-C₈-alkylcarbonylamino, a C₁-C₈-halogenoalkylcarbonylamino having 1 to5 halogen atoms, a C₁-C₈-alkylaminocarbonyloxy, adi-C₁-C₈-alkylaminocarbonyloxy, a C₁-C₈-alkyloxycarbonyloxy,C₁-C₈-alkylsulfenyl, a C₁-C₈-halogenoalkylsulfenyl having 1 to 5 halogenatoms, a C₁-C₈-alkylsulfinyl, a C₁-C₈-halogenoalkylsulfinyl having 1 to5 halogen atoms, C₁-C₈-halogenoalkylsulfinyl having 1 to 5 halogenatoms, a C₁-C₈-alkylsulfonyl, a C₁-C₈-halogenoalkylsulfonyl having 1 to5 halogen atoms, a C₁-C₆-alkoxyimino, a (C₁-C₆-alkoxyimino)-C₁-C₆-alkyl,a (C₁-C₆-alkenyloxyimino)-C₁-C₆-alkyl, a(C₁-C₆-alkynyloxyimino)-C₁-C₆-alkyl, a (benzyloxyimino)-C₁-C₆-alkyl, abenzyloxy, a benzylsulfanyl, a benzylamino, a phenoxy, a phenylsulfanyla phenyl, and a phenylamino; R¹ and R² are independently selected fromthe group consisting of a hydrogen atom, a cyano group, a formyl group,a carboxy group, a carbamoyl group, a (hydroxyimino)-C₁-C₆-alkyl group,a C₁-C₈-alkyl, a C₃-C₇-cycloalkyl-C₁-C₈-alkyl, a C₂-C₈-alkenyl, aC₂-C₈-alkynyl, a C₃-C₈-cycloalkyl, a C₃-C₈-halogenocycloalkyl having 1to 5 halogen atoms, a C₁-C₈-alkylcarbonyl, a C₁-C₈-halogenoalkylcarbonylhaving 1 to 5 halogen atoms, a C₁-C₈-halogenoalkyl having 1 to 5 halogenatoms, a C₁-C₈-alkylcarbamoyl, a di-C₁-C₈-alkylcarbamoyl, aC₁-C₈-alkoxycarbamoyl, a C₁-C₈-alkoxycarbonyl and aC₁-C₈-halogenoalkoxycarbonyl having 1 to 5 halogen atoms; R³ and R⁴ areindependently selected from the group consisting of a hydrogen atom, acyano group, a formyl group, a carboxy group, a carbamoyl group, a(hydroxyimino)-C₁-C₆-alkyl group, a C₁-C₈-alkyl,C₃-C₇-cycloalkyl-C₁-C₈-alkyl, a C₂-C₈-alkenyl, a C₂-C₈-alkynyl, aC₃-C₈-cycloalkyl, a C₃-C₈-halogenocycloalkyl having 1 to 5 halogenatoms, a C₁-C₈-alkylcarbonyl, a C₁-C₈-halogenoalkylcarbonyl having 1 to5 halogen atoms, a C₁-C₈-halogenoalkyl having 1 to 5 halogen atoms, aC₁-C₈-alkylcarbamoyl, a di-C₁-C₈-alkylcarbamoyl, aC₁-C₈-alkoxycarbamoyl, a C₁-C₈-alkoxycarbonyl, and aC₁-C₈-halogenoalkoxycarbonyl having 1 to 5 halogen atoms; R⁵ is selectedfrom the group consisting of a hydrogen atom, a C₁-C₆-alkyl, and aC₃-C₇-cycloalkyl; each Y is independently selected from the groupconsisting of a hydrogen atom, a halogen atom, a nitro group, a cyanogroup, a hydroxy group, an amino group, a sulfanyl group, apentafluoro-λ⁶-sulfanyl group, a formyl group, a formyloxy group, aformylamino group, a carboxy group, a carbamoyl group, aN-hydroxycarbamoyl group, a carbamate group, a(hydroxyimino)-C₁-C₆-alkyl group, a C₁-C₈-alkyl, a C₂-C₈-alkenyl, aC₂-C₈-alkynyl, a C₁-C₈-alkoxy, a C₁-C₈-halogenoalkyl having 1 to 5halogen atoms, a C₁-C₈-alkylsulfanyl, a C₁-C₈-halogenoalkylsulfanylhaving 1 to 5 halogen atoms, a C₂-C₈-alkenyloxy, aC₂-C₈-halogenoalkenyloxy having 1 to 5 halogen atoms, aC₃-C₈-alkynyloxy, a C₃-C₈-halogenoalkynyloxy having 1 to 5 halogenatoms, a C₃-C₈-cycloalkyl, a C₃-C₈-halogenocycloalkyl having 1 to 5halogen atoms, a C₁-C₈-alkylcarbonyl, a C₁-C₈-halogenoalkylcarbonylhaving 1 to 5 halogen atoms, a C₁-C₈-alkylcarbamoyl, adi-C₁-C₈-alkylcarbamoyl, a N—C₁-C₈-alkyloxycarbamoyl, aC₁-C₈-alkoxycarbamoyl, a N—C₁-C₈-alkyl-C₁-C₈-alkoxycarbamoyl, aC₁-C₈-alkoxycarbonyl, a C₁-C₈-halogenoalkoxycarbonyl having 1 to 5halogen atoms, a C₁-C₈-alkylcarbonyloxy, aC₁-C₈-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, aC₁-C₈-alkylcarbonylamino, a C₁-C₈-halogenoalkylcarbonylamino having 1 to5 halogen atoms, a C₁-C₈-alkylaminocarbonyloxy, adi-C₁-C₈-alkylaminocarbonyloxy, a C₁-C₈-alkyloxycarbonyloxy, aC₁-C₈-alkylsulfenyl, a C₁-C₈-halogenoalkylsulfenyl having 1 to 5 halogenatoms, a C₁-C₈-alkylsulfinyl, a C₁-C₈-halogenoalkylsulfinyl having 1 to5 halogen atoms, a C₁-C₈-alkylsulfonyl, a C₁-C₈-halogenoalkylsulfonylhaving 1 to 5 halogen atoms, a C₁-C₆-alkoxyimino, a(C₁-C₆-alkoxyimino)-C₁-C₆-alkyl, a (C₁-C₆-alkenyloxyimino)-C₁-C₆-alkyl,a (C₁-C₆-alkynyloxyimino)-C₁-C₆-alkyl and a(benzyloxyimino)-C₁-C₆-alkyl; and Y^(a) is selected from the groupconsisting of a halogen atom, a cyano group, a sulfanyl group, apentafluoro-λ⁶-sulfanyl group, a formyl group, a formyloxy group, aformylamino group, a carbamoyl group, a N-hydroxycarbamoyl group, acarbamate group, a (hydroxyimino)-C₁-C₆-alkyl group, a C₁-C₈-alkyl, aC₂-C₈-alkenyl, a C₂-C₈-alkynyl, a C₁-C₈-alkoxy, a C₁-C₈-halogenoalkylhaving 1 to 5 halogen atoms, a C₁-C₈-halogenoalkoxy having 1 to 5halogen atoms, a C₁-C₈-alkylsulfanyl, a C₁-C₈-halogenoalkylsulfanylhaving 1 to 5 halogen atoms, a C₂-C₈-halogenoalkenyloxy having 1 to 5halogen atoms, a C₃-C₈-alkynyloxy, a C₃-C₈-halogenoalkynyloxy having 1to 5 halogen atoms, a C₃-C₈-cycloalkyl, a C₃-C₈-halogenocycloalkylhaving 1 to 5 halogen atoms, a C₁-C₈-alkylcarbonyl, aC₁-C₈-halogenoalkylcarbonyl having 1 to 5 halogen atoms, aC₁-C₈-alkylcarbamoyl, a di-C₁-C₈-alkylcarbamoyl, aN—C₁-C₈-alkyloxycarbamoyl, a C₁-C₈-alkoxycarbamoyl, aN—C₁-C₈-alkyl-C₁-C₈-alkoxycarbamoyl, a C₁-C₈-alkoxycarbonyl, aC₁-C₈-halogenoalkoxycarbonyl having 1 to 5 halogen atoms, aC₁-C₈-alkylcarbonyloxy, a C₁-C₈-halogenoalkylcarbonyloxy having 1 to 5halogen atoms, a C₁-C₈-alkylcarbonylamino, aC₁-C₈-halogenoalkylcarbonylamino having 1 to 5 halogen atoms, aC₁-C₈-alkylaminocarbonyloxy, a di-C₁-C₈-alkylaminocarbonyloxy, aC₁-C₈-alkyloxycarbonyloxy, a C₁-C₈-alkylsulfenyl, aC₁-C₈-halogenoalkylsulfenyl having 1 to 5 halogen atoms, aC₁-C₈-alkylsulfinyl, a C₁-C₈-halogenoalkylsulfinyl having 1 to 5 halogenatoms, a C₁-C₈-alkylsulfonyl, a C₁-C₈-halogenoalkylsulfonyl having 1 to5 halogen atoms, a C₁-C₆-alkoxyimino, a (C₁-C₆-alkoxyimino)-C₁-C₆-alkyl,a (C₁-C₆-alkenyloxyimino)-C₁-C₆-alkyl, a(C₁-C₆-alkynyloxyimino)-C₁-C₆-alkyl, and a (benzyloxyimino)-C₁-C₆-alkyl;as well as its salts, N-oxides, and optically active isomers.
 2. Thecompound of claim 1, wherein n is 1 or
 2. 3. The compound of claim 1,wherein each X is independently selected from the group consisting of ahydrogen atom, a methyl group, a halogen atom, and a C₁-C₈-halogenoalkylhaving 1 to 5 halogen atoms.
 4. The compound of claim 1 wherein R¹ andR² are independently selected from the group consisting of a hydrogenatom, a C₁-C₈-alkyl, a C₂-C₈-alkenyl, a C₂-C₈-alkynyl, aC₃-C₈-cycloalkyl, a C₃-C₇-cycloalkyl-C₁-C₈-alkyl, aC₃-C₈-halogenocycloalkyl having 1 to 5 halogen atoms, and aC₁-C₈-halogenoalkyl having 1 to 5 halogen atoms.
 5. The compound ofclaim 1, wherein R³ and R⁴ are independently selected from the groupconsisting of a hydrogen atom, a C₁-C₈-alkyl, a C₂-C₈-alkenyl, aC₂-C₈-alkynyl, a C₃-C₈-cycloalkyl, a C₃-C₇-cycloalkyl-C₁-C₈-alkyl, aC₃-C₈-halogenocycloalkyl having 1 to 5 halogen atoms, and aC₁-C₈-halogenoalkyl having 1 to 5 halogen atoms.
 6. The compound ofclaim 1, wherein Y^(a) is selected from the group consisting of ahalogen atom, a pentafluoro-λ⁶-sulfanyl group, a C₁-C₈-alkyl, aC₁-C₈-halogenoalkyl having 1 to 5 halogen atoms, and aC₁-C₈-halogenoalkoxy having 1 to 5 halogen atoms.
 7. The compound ofclaim 1 wherein p is
 1. 8. The compound of claim 1, wherein each Y isindependently selected from the group consisting of a hydrogen atom anda halogen atom.
 9. The compound of claim 1, wherein A is substituted inthe 5-position.
 10. A process for the preparation of the compound ofclaim 1, which comprises reacting a heterocyclylethylamine derivative ofgeneral formula (II) or one of its salts:

in which A is a pyrimidine ring, each X is independently selected fromthe group consisting of a halogen atom, a nitro group, a cyano group, ahydroxy group, an amino group, a sulfanyl group, apentafluoro-λ⁶-sulfanyl group, a formyl group, a formyloxy group, aformylamino group, a carboxy group, a carbamoyl group, aN-hydroxycarbamoyl group, a carbamate group, a(hydroxyimino)-C₁-C₆-alkyl group, a C₁-C₈-alkyl, a C₂-C₈-alkenyl, aC₂-C₈-alkynyl, a C₁-C₈-alkylamino, a C₁-C₈-halogenoalkyl having 1 to 5halogen atoms, a di-C₁-C₈-alkylamino, a C₁-C₈-alkoxy, aC₁-C₈-halogenoalkoxy having 1 to 5 halogen atoms, a C₁-C₈-alkylsulfanyl,a C₁-C₈-halogenoalkylsulfanyl having 1 to 5 halogen atoms, aC₂-C₈-alkenyloxy, a C₂-C₈-halogenoalkenyloxy having 1 to 5 halogenatoms, a C₃-C₈-alkynyloxy, a C₂-C₈-halogenoalkynyloxy having 1 to 5halogen atoms, a C₃-C₈-cycloalkyl, a C₃-C₈-halogenocycloalkyl having 1to 5 halogen atoms, a C₁-C₈-alkylcarbonyl, a C₁-C₈-halogenoalkylcarbonylhaving 1 to 5 halogen atoms, a C₁-C₈-alkylcarbamoyl, adi-C₁-C₈-alkylcarbamoyl, a N—C₁-C₈-alkyloxycarbamoyl, aC₁-C₈-alkoxycarbamoyl, a N—C₁-C₈-alkyl-C₁-C₈-alkoxycarbamoyl, aC₁-C₈-alkoxycarbonyl, a C₁-C₈-halogenoalkoxycarbonyl having 1 to 5halogen atoms, a C₁-C₈-alkylcarbonyloxy, aC₁-C₈-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, aC₁-C₈-alkylcarbonylamino, a C₁-C₈-halogenoalkylcarbonylamino having 1 to5 halogen atoms, a C₁-C₈-alkylaminocarbonyloxy, adi-C₁-C₈-alkylaminocarbonyloxy, a C₁-C₈-alkyloxycarbonyloxy, aC₁-C₈-alkylsulfenyl, a C₁-C₈-halogenoalkylsulfenyl having 1 to 5 halogenatoms, a C₁-C₈-alkylsulfinyl, a C₁-C₈-halogenoalkylsulfinyl having 1 to5 halogen atoms, a C₁-C₈-alkylsulfonyl, a C₁-C₈-halogenoalkylsulfonylhaving 1 to 5 halogen atoms, a C₁-C₆-alkoxyimino, a(C₁-C₆-alkoxyimino)-C₁-C₆-alkyl, a (C₁-C₆-alkenyloxyimino)-C₁-C₆-alkyl,a (C₁-C₆-alkynyloxyimino)-C₁-C₆-alkyl, a (benzyloxyimino)-C₁-C₆-alkyl, abenzyloxy, a benzylsulfanyl, a benzylamino, a phenoxy, a phenylsulfanyla phenyl, and a phenylamino; n is 1, 2, or 3; z is a carbon atom whichcan not be substituted by X; R¹ and R² are independently selected fromthe group consisting of a hydrogen atom, a cyano group, a formyl group,a carboxy group, a carbamoyl group, a (hydroxyimino)-C₁-C₆-alkyl group,a C₁-C₈-alkyl, a C₃-C₇-cycloalkyl-C₁-C₈-alkyl, a C₂-C₈-alkenyl, aC₂-C₈-alkynyl, a C₃-C₈-cycloalkyl, a C₃-C₈-halogenocycloalkyl having 1to 5 halogen atoms, a C₁-C₈-alkylcarbonyl, a C₁-C₈-halogenoalkylcarbonylhaving 1 to 5 halogen atoms, a C₁-C₈-halogenoalkyl having 1 to 5 halogenatoms, a C₁-C₈-alkylcarbamoyl, a di-C₁-C₈-alkylcarbamoyl, aC₁-C₈-alkoxycarbamoyl, a C₁-C₈-alkoxycarbonyl, and aC₁-C₈-halogenoalkoxycarbonyl having 1 to 5 halogen atoms; R³ and R⁴ areindependently selected from the group consisting of a hydrogen atom, acyano group, a formyl group, a carboxy group, a carbamoyl group, a(hydroxyimino)-C₁-C₆-alkyl group, a C₁-C₈-alkyl,C₃-C₇-cycloalkyl-C₁-C₈-alkyl, a C₂-C₈-alkenyl, a C₂-C₈-alkynyl, aC₃-C₈-cycloalkyl, a C₃-C₈-halogenocycloalkyl having 1 to 5 halogenatoms, a C₁-C₈-alkylcarbonyl, a C₁-C₈-halogenoalkylcarbonyl having 1 to5 halogen atoms, a C₁-C₈-halogenoalkyl having 1 to 5 halogen atoms, aC₁-C₈-alkylcarbamoyl, a di-C₁-C₈-alkylcarbamoyl, aC₁-C₈-alkoxycarbamoyl, a C₁-C₈-alkoxycarbonyl, and aC₁-C₈-halogenoalkoxycarbonyl having 1 to 5 halogen, atoms; and R⁵ isselected from the group consisting of a hydrogen atom, a C₁-C₆-alkyl,and a C₃-C₇-cycloalkyl; with a carboxylic acid derivative of the generalformula (III)

in which: Y^(a) is selected from the group consisting of a halogen atom,a cyano group, a sulfanyl group, a pentafluoro-λ⁶-sulfanyl group, aformyl group, a formyloxy group, a formylamino group, a carbamoyl group,a N-hydroxycarbamoyl group, a carbamate group, a(hydroxyimino)-C₁-C₆-alkyl group, a C₁-C₈-alkyl, a C₁-C₃-alkenyl, aC₁-C₈-alkynyl, a C₁-C₃-alkoxy, a C₁-C₈-halogenoalkyl having 1 to 5halogen atoms, a C₁-C₈-halogenoalkoxy having 1 to 5 halogen atoms, aC₁-C₈-alkylsulfanyl, a C₁-C₈-halogenoalkylsulfanyl having 1 to 5 halogenatoms, a C₂-C₈-halogenoalkenyloxy having 1 to 5 halogen atoms, aC₁-C₈-alkynyloxy, a C₁-C₈-halogenoalkynyloxy having 1 to 5 halogenatoms, a C₁-C₈-cycloalkyl, a C₃-C₈-halogenocycloalkyl having 1 to 5halogen atoms, a C₁-C₈-alkylcarbonyl, a C₁-C₈-halogenoalkylcarbonylhaving 1 to 5 halogen atoms, a C₁-C₈-alkylcarbamoyl, adi-C₁-C₈-alkylcarbamoyl, a N—C₁-C₈-alkyloxycarbamoyl, aC₁-C₈-alkoxycarbamoyl, a N—C₁-C₈-alkyl-C₁-C₈-alkoxycarbamoyl, aC₁-C₈-alkoxycarbonyl, a C₁-C₈-halogenoalkoxycarbonyl having 1 to 5halogen atoms, a C₁-C₈-alkylcarbonyloxy, aC₁-C₈-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, aC₁-C₈-alkylcarbonylamino, a C₁-C₈-halogenoalkylcarbonylamino having 1 to5 halogen atoms, a C₁-C₈-alkylaminocarbonyloxy, adi-C₁-C₈-alkylaminocarbonyloxy, a C₁-C₈-alkyloxycarbonyloxy, aC₁-C₈-alkylsulfenyl, C₁-C₈-halogenoalkylsulfenyl having 1 to 5 halogenatoms, a C₁-C₈-alkylsulfinyl, a C₁-C₈-halogenoalkylsulfinyl having 1 to5 halogen atoms, a C₁-C₈-alkylsulfonyl, C₁-C₈-halogenoalkylsulfonylhaving 1 to 5 halogen atoms, a C₁-C₆-alkoxyimino, a(C₁-C₆-alkoxyimino)-C₁-C₆-alkyl, a (C₁-C₆-alkenyloxyimino)-C₁-C₆-alkyl,a (C₁-C₆-alkynyloxyimino)-C₁-C₆-alkyl, a (benzyloxyimino)-C₁-C₆-alkyl: Yis the same or different and is a hydrogen atom, a halogen atom, a nitrogroup, a cyano group, a hydroxy group, an amino group, a sulfanyl group,a pentafluoro-λ⁶-sulfanyl group, a formyl group, a formyloxy group, aformylamino group, a carboxy group, a carbamoyl group, aN-hydroxycarbamoyl group, a carbamate group, a(hydroxyimino)-C₁-C₆-alkyl group, a C₁-C₈-alkyl, a C₂-C₈-alkenyl, aC₂-C₈-alkynyl, a C₁-C₈-alkoxy, a C₁-C₈-halogenoalkyl having 1 to 5halogen atoms, a C₁-C₈-alkylsulfanyl, a C₁-C₈-halogenoalkylsulfanylhaving 1 to 5 halogen atoms, a C₂-C₈-alkenyloxy, aC₂-C₈-halogenoalkenyloxy having 1 to 5 halogen atoms, aC₃-C₈-alkynyloxy, a C₃-C₈-halogenoalkynyloxy having 1 to 5 halogenatoms, a C₃-C₈-cycloalkyl, a C₃-C₈-halogenocycloalkyl having 1 to 5halogen atoms, a C₁-C₈-alkylcarbonyl, a C₁-C₈-halogenoalkylcarbonylhaving 1 to 5 halogen atoms, a C₁-C₈-alkylcarbamoyl, adi-C₁-C₈-alkylcarbamoyl, a N—C₁-C₈-alkyloxycarbamoyl, aC₁-C₈-alkoxycarbamoyl, a N—C₁-C₈-alkyl-C₁-C₈-alkoxycarbamoyl, aC₁-C₈-alkoxycarbonyl, a C₁-C₈-halogenoalkoxycarbonyl having 1 to 5halogen atoms, a C₁-C₈-alkylcarbonyloxy, aC₁-C₈-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, aC₁-C₈-alkylcarbonylamino, a C₁-C₈-halogenoalkylcarbonylamino having 1 to5 halogen atoms, a C₁-C₈-alkylaminocarbonyloxy, adi-C₁-C₈-alkylaminocarbonyloxy, a C₁-C₈-alkyloxycarbonyloxy, aC₁-C₈-alkylsulphenyl, a C₁-C₈-halogenoalkylsulphenyl having 1 to 5halogen atoms, a C₁-C₈-alkylsulphinyl, a C₁-C₈-halogenoalkylsulphinylhaving 1 to 5 halogen atoms, a C₁-C₈-alkylsulphonyl, aC₁-C₈-halogenoalkylsulphonyl having 1 to 5 halogen atoms, aC₁-C₆-alkoxyimino, a (C₁-C₆-alkoxyimino)-C₁-C₆-alkyl, a(C₁-C₆-alkenyloxyimino)-C₁-C₆-alkyl, a(C₁-C₆-alkynyloxyimino)-C₁-C₆-alkyl, and a (benzyloxyimino)-C₁-C₆-alkyl;and p is 1, 2, 3 or 4; L¹ is a leaving group selected from the groupconsisting of a halogen atom, a hydroxyl group, —OR²³, and —OCOR²³;wherein R²³ is selected from the group consisting of a C₁-C₆ alkyl, aC₁-C₆ haloalkyl, a benzyl, 4-methoxybenzyl, pentafluorophenyl, and agroup of formula:

in the presence of a catalyst and, if L¹ is a hydroxyl group, in thepresence of a condensing agent.
 11. The process of claim 10, wherein R⁵is a hydrogen atom, and the process is completed by a further stepaccording to the following reaction scheme:

in which: A is a pyrimidine ring; each X is selected from the groupconsisting of a halogen atom, a nitro group, a cyano group, a hydroxygroup, an amino group, a sulfanyl group, a pentafluoro-λ⁶-sulfanylgroup, a formyl group, a formyloxy group, a formylamino group, a carboxygroup, a carbamoyl group, a N-hydroxycarbamoyl group, a carbamate group,a (hydroxyimino)-C₁-C₆-alkyl group, a C₁-C₈-alkyl, a C₂-C₈-alkenyl, aC₂-C₈-alkynyl, a C₁-C₈-alkylamino, a C₁-C₈-halogenoalkyl having 1 to 5halogen atoms, a di-C₁-C₈-alkylamino, a C₁-C₈-alkoxy, aC₁-C₈-halogenoalkoxy having 1 to 5 halogen atoms, a C₁-C₈-alkylsulfanyl,a C₁-C₈-halogenoalkylsulfanyl having 1 to 5 halogen atoms, aC₂-C₈-alkenyloxy, a C₂-C₈-halogenoalkenyloxy having 1 to 5 halogenatoms, a C₃-C₈-alkynyloxy, a C₃-C₈-halogenoalkynyloxy having 1 to 5halogen atoms, a C₃-C₈-cycloalkyl, a C₃-C₈-halogenocycloalkyl having 1to 5 halogen atoms, a C₁-C₈-alkylcarbonyl, a C₁-C₈-halogenoalkylcarbonylhaving 1 to 5 halogen atoms, a C₁-C₈-alkylcarbamoyl, adi-C₁-C₈-alkylcarbamoyl, a N—C₁-C₈-alkyloxycarbamoyl, aC₁-C₈-alkoxycarbamoyl, a N—C₁-C₈-alkyl-C₁-C₈-alkoxycarbamoyl, aC₁-C₈-alkoxycarbonyl, a C₁-C₈-halogenoalkoxycarbonyl having 1 to 5halogen atoms, a C₁-C₈-alkylcarbonyloxy, aC₁-C₈-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, aC₁-C₈-alkylcarbonylamino, a C₁-C₈-halogenoalkylcarbonylamino having 1 to5 halogen atoms, a C₁-C₈-alkylaminocarbonyloxy, adi-C₁-C₈-alkylaminocarbonyloxy, a C₁-C₈-alkyloxycarbonyloxy, aC₁-C₈-alkylsulfenyl, a C₁-C₈-halogenoalkylsulfenyl having 1 to 5 halogenatoms, a C₁-C₈-alkylsulfinyl, a C₁-C₈-halogenoalkylsulfinyl having 1 to5 halogen atoms, a C₁-C₈-alkylsulfonyl, a C₁-C₈-halogenoalkylsulfonylhaving 1 to 5 halogen atoms, a C₁-C₆-alkoxyimino, a(C₁-C₆-alkoxyimino)-C₁-C₆-alkyl, a (C₁-C₆-alkenyloxyimino)-C₁-C₆-alkyl,a (C₁-C₆-alkynyloxyimino)-C₁-C₆-alkyl, a (benzyloxyimino)-C₁-C₆-alkyl, abenzyloxy, a benzylsulfanyl, a benzylamino, a phenoxy, a phenylsulfanyla phenyl, and a phenylamino; n is 1, 2, or 3; z is a carbon atom whichcan not be substituted by X: R¹ and R² are independently selected fromthe group consisting of a hydrogen atom, a cyano group, a formyl group,a carboxy group, a carbamoyl group, a (hydroxyimino)-C₁-C₆-alkyl group,a C₁-C₈-alkyl, a C₃-C₈-cycloalkyl-C₁-C₈-alkyl, a C₂-C₈-alkenyl, aC₂-C₈-alkynyl, a C₃-C₈-cycloalkyl, a C₃-C₈-halogenocycloalkyl having 1to 5 halogen atoms, a C₁-C₈-alkylcarbonyl, a C₁-C₈-halogenoalkylcarbonylhaving 1 to 5 halogen atoms, a C₁-C₈-halogenoalkyl having 1 to 5 halogenatoms, a C₁-C₈-alkylcarbamoyl, a di-C₁-C₈-alkylcarbamoyl, aC₁-C₈-alkoxycarbamoyl, a C₁-C₈-alkoxycarbonyl, and aC₁-C₈-halogenoalkoxycarbonyl having 1 to 5 halogen atoms; R³ and R⁴ areindependently selected from the group consisting of a hydrogen atom, acyano group, a formyl group, a carboxy group, a carbamoyl group, a(hydroxyimino)-C₁-C₆-alkyl group, a C₁-C₈-alkyl,C₃-C₇-cycloalkyl-C₁-C₃-alkyl, a C₂-C₈-alkenyl, a C₂-C₈-alkynyl, aC₁-C₈-cycloalkyl, a C₁-C₈-halogenocycloalkyl having 1 to 5 halogenatoms, a C₁-C₈-alkylcarbonyl, a C₁-C₈-halogenoalkylcarbonyl having 1 to5 halogen atoms, a C₁-C₈-halogenoalkyl having 1 to 5 halogen atoms, aC₁-C₈-alkylcarbamoyl, a di-C₁-C₈-alkylcarbamoyl, aC₁-C₈-alkoxycarbamoyl, a C₁-C₈-alkoxycarbonyl, and aC₁-C₈-halogenoalkoxycarbonyl having 1 to 5 halogen atoms; Y^(a) isselected from the group consisting of a halogen atom, a cyano group, asulfanyl group, a pentafluoro-λ⁶-sulfanyl group, a formyl group, aformyloxy group, a formylamino group, a carbamoyl group, aN-hydroxycarbamoyl group, a carbamate group, a(hydroxyimino)-C₁-C₆-alkyl group a C₁-C₈-alkyl, a C₂-C₈-alkenyl, aC₂-C₈-alkynyl, a C₁-C₈-alkoxy, a C₁-C₈-halogenoalkyl having 1 to 5halogen atoms, a C₁-C₈-halogenoalkoxy having 1 to 5 halogen atoms, aC₁-C₈-alkylsulfanyl, a C₁-C₈-halogenoalkylsulfanyl having 1 to 5 halogenatoms, a C₂-C₈-halogenoalkenyloxy having 1 to 5 halogen atoms, aC₃-C₈-alkynyloxy, a C₃-C₈-halogenoalkynyloxy having 1 to 5 halogenatoms, a C₃-C₈-cycloalkyl, a C₁-C₈-halogenocycloalkyl having 1 to 5halogen atoms, a C₁-C₈-alkylcarbonyl, a C₁-C₈-halogenoalkylcarbonylhaving 1 to 5 halogen atoms, a C₁-C₈-alkylcarbamoyl, adi-C₁-C₈-alkylcarbamoyl, a N—C₁-C₈-alkyloxycarbamoyl, aC₁-C₈-alkoxycarbamoyl, a N—C₁-C₈-alkyl-C₁-C₈-alkoxycarbamoyl, aC₁-C₈-alkoxycarbonyl, a C₁-C₈-halogenoalkoxycarbonyl having 1 to 5halogen atoms, a C₁-C₈-alkylcarbonyloxy, aC₁-C₈-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, aC₁-C₈-alkylcarbonylamino, a C₁-C₈-halogenoalkylcarbonylamino having 1 to5 halogen atoms, a C₁-C₈-alkylaminocarbonyloxy, adi-C₁-C₈-alkylaminocarbonyloxy, a C₁-C₈-alkylsulfenyl, aC₁-C₈-halogenoalkylsulfenyl having 1 to 5 halogen atoms, aC₁-C₈-alkylsulfinyl, a C₁-C₈-halogenoalkylsulfinyl having 1 to 5 halogenatoms, a C₁-C₈-alkylsulfonyl, a C₁-C₈-halogenoalkylsulfonyl having 1 to5 halogen atoms, a C₁-C₆-alkoxyimino, a (C₁-C₆-alkoxyimino)-C₁-C₆-alkyl,a (C₁-C₆-alkenyloxyimino)-C₁-C₆-alkyl, a(C₁-C₆-alkynyloxyimino)-C₁-C₆-alkyl, a (benzyloxyimino)-C₁-C₆-alkyl;each Y is independently selected from the group consisting of a hydrogenatom, a halogen atom, a nitro group, a cyano group, a hydroxy group, anamino group, a sulfanyl group, a pentafluoro-λ⁶-sulfanyl group, a formylgroup, a formyloxy group, a formylamino group, a carboxy group, acarbamoyl group, a N-hydroxycarbamoyl group, a carbamate group, a(hydroxyimino)-C₁-C₆-alkyl group, a C₁-C₈-alkyl, a C₂-C₈-alkenyl, aC₂-C₈-alkynyl, a C₁-C₈-alkoxy, a C₁-C₈-halogenoalkyl having 1 to 5halogen atoms, a C₁-C₈-alkylsulfanyl, a C₁-C₈-halogenoalkylsulfanylhaving 1 to 5 halogen atoms, a C₂-C₈-alkenyloxy, aC₂-C₈-halogenoalkenyloxy having 1 to 5 halogen atoms, aC₃-C₈-alkynyloxy, a C₃-C₈-halogenoalkynyloxy having 1 to 5 halogenatoms, a C₃-C₈-cycloalkyl, a C₃-C₈-halogenocycloalkyl having 1 to 5halogen atoms, a C₁-C₈-alkylcarbonyl, a C₁-C₈-halogenoalkylcarbonylhaving 1 to 5 halogen atoms, a C₁-C₈-alkylcarbamoyl, adi-C₁-C₈-alkylcarbamoyl, a N—C₁-C₈-alkyloxycarbamoyl, aC₁-C₈-alkoxycarbamoyl, a N—C₁-C₈-alkyl-C₁-C₈-alkoxycarbamoyl, aC₁-C₈-alkoxycarbonyl, a C₁-C₈-halogenoalkoxycarbonyl having 1 to 5halogen atoms, a C₁-C₈-alkylcarbonyloxy, aC₁-C₈-halogenoalkylcarbonyloxy having 1 to 5 halogen atoms, aC₁-C₈-alkylcarbonylamino, a C₁-C₈-halogenoalkylcarbonylamino having 1 to5 halogen atoms, a C₁-C₈-alkylaminocarbonyloxy, adi-C₁-C₈-alkylaminocarbonyloxy, a C₁-C₈-alkyloxycarbonyloxy, aC₁-C₈-alkylsulfenyl, a C₁-C₈-halogenoalkylsulfenyl having 1 to 5 halogenatoms, a C₁-C₈-alkylsulfinyl, a C₁-C₈-halogenoalkylsulfinyl having 1 to5 halogen atoms, a C₁-C₈-alkylsulfonyl, a C₁-C₈-halogenoalkylsulfonylhaving 1 to 5 halogen atoms, a C₁-C₆-alkoxyimino, a(C₁-C₆-alkoxyimino)-C₁-C₆-alkyl, a (C₁-C₆-alkenyloxyimino)-C₁-C₆-alkyl,a (C₁-C₆-alkynyloxyimino)-C₁-C₆-alkyl, and a(benzyloxyimino)-C₁-C₆-alkyl; p is 1, 2, 3 or 4; R^(5a) is selected fromthe group consisting of a C₁-C₆-alkyl, and a C₃-C₇-cycloalkyl; and L² isa leaving group selected from the group consisting of a halogen atom, a4-methyl phenylsulfonyloxy, and a methylsulfonyloxy; comprising reactinga compound of formula (Ia) with a compound of formula (III) to provide acompound of formula (I).
 12. A fungicide composition comprising aneffective amount of the compound of claim 1 and an agriculturallyacceptable support.
 13. A method for combating the phytopathogenic fungiof crops comprising applying an effective and non-phytotoxic amount ofthe fungicide composition of claim 12 to the plant seeds or to the plantleaves and/or to the fruits of the plants or to the soil in which theplants are growing or in which it is desired to grow them.